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'First, Let's Get Rid of All the Bosses' -- the Zappos Management Experiment
schnell writes: The New Republic is running an in-depth look at online shoe retailer Zappos.com's experiment in a new "boss-less" corporate structure. Three years ago the company introduced a management philosophy that came from the software development world called "Holacracy," in which there are no "people managers" and groups self-organize based on individual creativity and talents. (When the change was announced, 14% of the company's employees chose to leave; middle management openly rebelled, but perhaps surprisingly the tech organization was slowest to embrace the new idea). The article shows that in this radically employee-centric environment, many if not most employees are thrilled and fulfilled, while others worry that self-organization in practical terms means chaos and a Maoist culture of "coercive positivity." Is Zappos the future of the American workplace, a fringe experiment, or something in between?
Protip: you don't have to have a boss to have somebody working the management function you describe.
That's the part people are missing; the vast majority of management functions do not require a person with nearly unlimited power and discretion over the other workers involved. A team can simply have a "external liaison" hat that somebody has to wear, and whoever is currently assigned that function does the "explaining to the suits what is possible and what isn't." In your example, I see no utility at all in involving a boss. If there is a project lead who is not only a technical lead, but actually a boss, they would actually be well-served having an assistant who can do grunt work like explaining possibilities of engineering to suits. That said, most of the projects I've been on do not have a boss inside the team at all; the worst the team leader could do is the same that any other team member could do; write an email to a suit. Instead, the team leader is the one designated to have authority over what goes into the source repository, the technical requirements for those things, and to tie-break the who-does-what when everybody wants the same toy.
Conflating bossing with the management of a resource is the base of the problem. If there is truly a conflict of interest between what the team wants and what an individual worker does, that can be dealt with in a separate process than is used for managing team resources. In fact, once that sort of issue comes up and there is that much conflict, the worker just needs to get fired (or transferred, re-educated, etc, depending on your societal norms) and that can be done by a vote; there is no requirement to have a Boss even to decide who gets hired and fired.
Of course, all of that works only when workers have a high enough morale to support a healthy work ethic. If there is high turnover then it will be Lord of the Flies. But if it is well-paid professionals, who value the work they do personally, and the work the company does, then it can run very smoothly. (I use "professional" to describe people who take their career seriously, not just white collar workers with letters)